


Life Imitates Art

by NeverEverAfter



Category: Supernatural
Genre: Dirty Talk, F/M, One Shot, Quickies, Reader-Insert, Semi-Public Sex, Smut, Swearing, Vaginal Sex
Language: English
Status: Completed
Published: 2015-09-16
Updated: 2015-09-16
Packaged: 2018-04-21 00:56:07
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,366
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4808774
Author URL: https://archiveofourown.org/users/NeverEverAfter/pseuds/NeverEverAfter
Summary: <blockquote class="userstuff">
              <p>Written for the prompt: Imagine Dean finding you reading fanfiction and deciding to reenact some things to show how much better he is.</p><p>Dean, Sam, and you crash the Third Annual Supernatural Convention, hoping to hook yourselves up with some much needed Leviathan intel. When you stumble across one website’s risque interpretations of the friendship between you and Dean, the two of you find yourselves hooking up in other ways. (Story takes place in the middle of Season 7.)</p>
            </blockquote>





	Life Imitates Art

**Author's Note:**

> Y/N = Your Name

Through the cracked door of the motel bathroom, you can hear the Winchesters discussing the latest mission concerning the world's growing Leviathan problem. “The world's problem,” of course means “your ragtag family's problem.” And as for “discussing,” well... “Bickering about it” may be the more accurate description. Naturally.

“I don't even get why we're going to this thing,” Dean grouses. “The first one was a heaping dinner portion of awkward. I'm not exactly in the mood for seconds.”

Sam's exhausted sigh is so telling that you can practically hear the eye roll in it. “Me either, Dean, but we've been spinning our tires for weeks. A lead is a lead. And if you're so gung-ho about taking down Dick Roman, this is the best we've got.”

Even without seeing the look on Dean's face, you know that the truth in Sam's words must have him fuming. Dean had been committed to the cause before, but now? Now it's personal. He wants big daddy Leviathan's head on a pike. Matter of fact, he _burns_ for it. But he still doesn't have to like that this latest endeavor is the only game in town, and he sure as hell doesn't have to pretend to be happy about it.

“Yeah, that's another thing. Who the hell plans these?” The sound of booted footfalls as Dean drags his feet along the floor. “Pineview was actually haunted and this place is a—a friggin' _Dick sandwich_.”

Colorful wording, but otherwise accurate. Your intended destination is located smack dab in the middle of two small businesses recently gobbled up—no pun intended—by none other than Richard Roman Enterprises. Whoever organizes these things has a knack for either bad luck or bad decisions. Probably both.

On the other hand...

“There's an upside to this, guys,” you chirp, making your way out of the bathroom. “Incognito behind enemy lines. I mean, if _I_ were a Leviathan, the Third Annual Supernatural Convention would be the last place I'd expect to find us.”

“Well, you're not wro—” Dean stops his pacing and does a double-take. “Y/N, what the hell are you wearing?”

“Check it out,” you say with a proud grin, gesturing to your attire with one hand while holding out a used copy of _Supernatural_ with the other. You tap your finger over a woman on the cover who is clearly meant to be _you_. “In character and everything.”

Unlike Dean, you've been channeling your grief through the “grin and bear it” method. It devastates you to see the boys brought so low by Bobby's death, and you hope with everything in you that a cheerful attitude might raise morale—jokes, smiles, laughter. That's the idea anyway. Sometimes it backfires—okay, a lot of the time it backfires—but no one can say you don't try.

Sam looks your way, sucking in a deep breath through his nose. “Yeah, I think I'm with Dean on this one,” he says through his exhale, hazel eyes flicking back and forth between you and your likeness. “You are way too okay with this.”

“Come on, guys,” you whine, the emphasis comically overdone. “Where's your sense of humor?” Even they should be able to admit that real you going undercover as fake you is just the slightest bit funny. Then again, you'd found your archangel-induced foray into TV Land circa 2009 _hilarious_ , so maybe your perspective on the matter is a tad unique.

“I'm checking mine at the door,” Dean deadpans, “Along with your sense of pride.”

“ _Ouch_.” You feign being affronted, knitting your brows together and bringing a hand to your chest.

“Do they actually think you hunt—in _that_?” Sam asks, taking the book from you and giving it an incredulous shake before tossing it onto the bed. The outfit in question is a jean skirt (far too short to be allowed in polite society), a cropped black halter, and an over-sized plaid button-up—one of Dean's, to be exact—left unfastened but tied together at your waist using the loose corners of fabric. “I mean, it's not exactly...” He pauses and sighs, rubbing a thumb against the scar on his palm. “...Practical.”

For what it's worth, Sam's right, but dear lord—on one point at least, you're convinced the artist had an eye for quality. You'd never appreciated just how _good_ Dean smells until today, wrapped in his shirt, the musky scent of his aftershave still clinging to the collar. Better to keep that particular observation to yourself though. After all, your relationship with the older Winchester is platonic. Totally platonic. Absolutely. One hundred and ten percent.

“Doubt it.” You force a break in your own reverie and respond to Sam's question with a smile. “But what can I say? Sex sells, right?” Not that you'd be thinking about sex at a time like this. No, never. You've got far more important things to—

“Let's just get this over with,” Dean groans as he heads for the door, swinging it open and gesturing an “after you” with his hand. "Standing around with Daisy Duke here is giving me a serious case of secondhand embarrassment.”

“Oh, _ha-ha_.” Thank god for sarcasm. You smack a retaliatory hand against his—firm, toned, stop thinking about it—chest as you stroll past and situate yourself in the back seat of Team Free Will's nondescript car-of-the-week. For the duration of the ride, you maintain a strict silence. I mean, really? “Secondhand embarrassment?” Your disappointment is another thing that's best kept secret.

As it turns out, there's a twisted sort of fascination that follows when the author of an occult-fantasy book series mysteriously drops off the face of the earth. In the two years following the aversion of the apocalypse, Chuck's—that is, Carver Edlund's— _Supernatural_ novels had developed something of a cult following. Bolstered by a new influx of fans, the Third Annual Supernatural Convention had promised enough of a turn-out that it warranted a weekend event.

Combine that with the fact that the host venue _just so happens_ to fall between two fresh hot spots of big-mouth activity, and suddenly your little group of freedom fighters is presented with a unique opportunity for gathering intel: three whole days to bug the buildings, stash the receivers in a central location, and wait for the incriminating details to roll in.

Hell, even if the Levis did manage to pick the bugs, the furthest they could track you would be their own next-door neighbor. Right into a veritable zebra herd of Winchester lookalikes—random civis in a heavily traversed public place, strictly off-limits for consumption at this stage in the Leviathan game.

God himself could not have reached down from the heavens to grant you a better solid than that. Despite how Dean feels about the location, this turn of events is a windfall—one small oasis of _maybe_ in a vast desert of _nada_ and _bubkes_. You guys _need_ this.

Dean pulls into the parking lot at ground zero, grumbling under his breath about “cheap imitations” and the vast unfairness of the world when the only available space falls between two black Impalas—replicas of his beloved Baby. If you can say nothing else about your group's unwitting admirers, they're dedicated to a fault. Dean isn't half as impressed, giving a spiteful farewell slam to the door of the little red junker.

Upon reaching the front door of the convention center Sam clenches his jaw and swallows hard. “I'll just—scout the perimeter. Case the alleys. Find some entry points; fire escapes, maybe.”

You fight against your own amusement at the younger Winchester's rambling, your noble but unsuccessful attempt at stifling a smile. All unfortunate run-in possibilities considered, Sam is far less terrified of a hungry Leviathan than he is of his number one fan. Following the Vegas incident, use of her name is expressly forbidden.

“Recon only, Sammy,” Dean says, leveling his eyes at his brother. “Nobody makes a move until we regroup.”

“Yeah,” Sam snaps. You can't tell if he's irritated or just ready to get the hell outta there. Probably both. “Got it.” He turns on his heels, walking away at an impressive clip without sparing a single glance back.

“I guess that means it's down the rabbit hole for us, huh?” You nudge Dean with your shoulder, earning you a resigned sigh.

“In and out,” he says in a deep undertone. “The faster the better.”

God, does he even listen to himself? Dean “Sex-on-Legs” Winchester. Nice to meet you.

Inside, the lobby and main hall are swarming with costumed fans. An army of demons. Monsters of every description. Knock-off Sams and Deans as far as the eye can see. You, you, and more you. As the two of you attempt to navigate the waves, an unobservant pseudo-Bobby sporting a trucker hat and a fake beard knocks shoulders with Dean, spouting off a good-natured “Watch where you're going, ya idjit!” as he passes.

Intuitively, you look to Dean, noting the barely contained fire behind his eyes and the hard set of his jaw as he bites down on the misplaced rage. Two weeks ago he might have taken a swing at the poor, unsuspecting son of a bitch on the spot. Believe it or not, this is progress. You place a gentle hand at the small of his back in an attempt at comfort.

“I'm gonna get a drink,” he mutters, not giving you a chance to respond before heading off in the direction of the cash bar. There was a time you might have been offended at Dean leaving you to do the grunt work, but given the circumstances, you can't find it in your heart to complain. Paint-by-numbers tech installation isn't exactly rocket science anyway, so if he needs a breather, you'll let him have it.

Truth be told, you'd give him just about anything.

Ground level is flooded with people, eyes everywhere, and you want something covert. Ascending the nearest staircase, you leave the bulk of the activity behind you, finding the second floor to be far more suitable in terms of traffic. Lack thereof, in this case. You check each room systematically, scoping out a workable place for a makeshift monitoring station. At the end of the first hall, you find a door slightly ajar, light still on, and you peek your head in.

Computer center. Awesome. Perfect place to hide a little extra hardware.

After a quick survey of the room to be sure it's empty, you make your way to one of the far corners and unshoulder your pack, digging through a change of clothes to get to the surveillance equipment. It doesn't take more than a few minutes to have everything hooked up and adequately camouflaged—this isn't your first rodeo. You snatch up your bag, now much lighter without the bulk of its cargo, and make your way back to the door.

Step one, complete. Now for the fun part: reconvene with Dean and Sam, plant the cameras and mics in the neighboring buildings, run a field test on the equipment, and wait. With any luck, Monday's score will be Team Free Will: 1, Chompers: 0.

You are just about to exit the room, when something on the computer closest to the door catches your eye— _your name_ , right there in black and white, near the top of the screen:

_Y/N is a Dean Girl._

“Okay,” you breathe, wide-eyed, as you pull out the swivel chair and take a seat. You have no idea how this website seems to be reading the entire state your freaking mind tonight, but color yourself intrigued. “You got me. Tell me more.”

What you discover, as the minutes tick by and you find yourself scrolling further and further down the page, turns out to be a lot, _lot_ more. It's a story—one of many, cached together in an archive—that describes any number of lascivious acts, starring Dean and yourself as the romantic leads.

You. And Dean Winchester. Holy crap.

Link after link after godforsaken link of the same, and you can't stop clicking. Apparently, your fictional sins are legion: Dean going down on you in the back of the Impala, you returning the favor with both of you in full FBI regalia, _31 freaking flavors_ of sex positions with no detail spared for any of them. Honestly, it's just a little bit creepy that a graphic Dean-slash-Y/N erotica library exists. Online. For all the world to see.

But even more honestly? It's so fucking hot.

You'd be lying if you said you weren't curious. Shit, at this point you are _dying_ to know what some of these things you're reading would feel like. Dean tying you up and taking you dirty, Dean lying back and watching you ride him like the world was ending, Dean pushing you up against the wall and fucking you for all you're worth, Dean—

“So, we done here? Please tell me we're done here.”

_Dean._

You nearly jump out of your seat at the sound of his voice, your brain scrambling in a futile attempt to maintain any semblance of dignity.

“I thought you were getting a drink!” you blurt out, sounding every ounce as horrified as you are, a furious blush rising in your cheeks as he walks over.

“I've had _three_ ,” he corrects, now standing directly beside you, eyes scanning the page. “...Is that _porn_?”

Shit. You are caught. He caught you. You are so fucking doomed. You've survived through hell and high water only to make it to this moment, to end in shame. You can just see it now, carved into your tombstone in big, bold letters: _Here lies Y/N. She was a Dean Girl._

You cover your flushed face with your hands, halfway to the grave already. “Would you believe me if I told you I found it like this?” God help you, you sound positively desperate, but it's the truth. More or less.

For a long time—or what damn well feels like it when you are dying a slow, embarrassing death—he doesn't answer, and you don't dare look at him. Just when you think it can't possibly get any worse, _it does_.

“This the kinda stuff you're into, Y/N?”

“What stuff?” you groan, finally dragging your hands down your cheeks and glancing over at him. If this is your sword, you may as well fall on it. “You mean the painfully awkward kind?”

“No,” he says, voice gruff, “the _me_ kind.”

When his eyes meet yours, you could almost swear that you see a faint sparkle of mischief in them, a quirky upturn at the corner of his mouth. No way. Your mind is currently so far off the reservation that you've gotta be imagining things, seeing what you want to see. In your wildest dreams a smile would make sense, but in reality? _Tonight?_ Every thread of logic you can find leads to the fact—because it's gotta be fact, right?—that he's in no mood for games.

“Are you—you're _really_ asking me that— _right_ now?” You swivel away, shoving yourself up from the chair and circling back around Dean. Anything to avoid direct eye contact, and the exit looks particularly appealing. “You can't be serious.”

“As a heart attack,” he says, uncrossing his arms and turning toward you. “Y'know, I'd be lyin' if I said I hadn't thought about it.”

Speaking of heart attacks...

“'Thought about it,'” you repeat quietly, angling yourself away from him and forcing a swallow despite the sudden dryness of your mouth. “You mean about us?”

“Once or twice.” The rough timbre of his voice is music to your ears. It makes everything sound better, even words that are perfect to begin with. When your stunned silence doesn't become anything more, Dean clears his throat expectantly. “You?”

“Yeah,” you huff, finding it easier to speak when not under the captivating influence of those gorgeous eyes. Too easy perhaps, as the unabridged admission comes tumbling out of your mouth: “Maybe a little more than twice.”

From behind you, you can hear him shift and move closer, feel his chest press against your shoulder as he reaches around to shut the door, punctuating his intent with a _click_. Hell, if that's how it's gonna be, you can't say you're opposed, though your courage is still one step behind.

As the weak flesh catches up to the willing spirit, you turn around and tilt your head back up to Dean. A tentative utterance of his name barely leaves your lips before he seals them with his own. It feels out of place almost—but perfectly so—to have him leaning over you, cupping your face in his hands. With a soft brush of his thumbs against your jaw, he prompts you to open your mouth for him. And why wouldn't you? God, you'd been thinking about it all evening...

His tongue is gentle and warm against your own, the taste of him laced with the subtle sweetness of bourbon. He guides you backward; one step, then two until you feel the stalwart support of the wall behind you—appropriate, given the sudden weakness in your knees. You moan against him, adding a depth to the kiss that equals your desire, and hook your fingers into the pockets of his jeans, pulling his hips—and everything in between—close against your body.

The added pressure against his already growing erection is enough to draw a groan from him. He lowers his hands to your waist, tracing strong fingers along the skin at the low-rise line of your skirt.

“You okay with this?” he asks in a low murmur, breaking the kiss and letting his forehead rest against yours.

“Yeah,” you manage, almost breathless. “Dean. Yes.”

“In that case...” He glides his hands up your torso, lifting the snug fabric of your halter over your breasts before skimming the exposed flesh with his fingertips, then his palms. “I'm thinking we make it quick now,” Another kiss, his hot breath washing over your lips, which are now trembling with anticipation. “And take our time later. Sound good?”

So fucking good.

The responsible part of you—rapidly shrinking as Dean gives both of your pert nipples a light pinch between his fingers—is aware that you have a job to do. Aware that there are hundreds of clueless civilians milling around downstairs. That _Sam_ is probably out on the sidewalk, checking his watch with growing impatience, while you are busy whimpering under his brother's gun-calloused hands and full lips. Every other part, heedless and wanting, pushes back against Dean's touch in emphatic agreement.

Make it quick now. Take our time later.

 _God_ , you can hardly stand it, the heat between your thighs rising by the second.

“I've heard a lot about you, Dean Winchester,” you tease, regathering your pride. You explore the smooth muscles of his abdomen with your fingers, starting with the sleek v-line at his hips and working your way up. “Think you can live up to the hype?”

He reluctantly pulls his hands away and places his palms against the wall at either side of you, allowing you unrestricted access to his body. You ache for the loss, but his physical response to your roaming touch more than compensates—swift rises and falls of his chest and abs, following in earnest after the wake of your caresses.

“The real deal's better,” he says, voice deepened with lust. “I promise.”

Not difficult to believe. In theory, Dean is amazing; in the flesh, he's a whole other animal.

“So cocky," you purr, making quick work of his belt buckle, button, and fly. His breath hitches when you slip one small hand into his jeans, letting it rest in the promising space between his thigh and his hardened length, a tantalizing proximity that goads him into action.

"One way of puttin' it,” he growls with a vehement jut of his hips, a forceful relocation of your hand from where it was to where he needs it to be. No better reminder than the rigid swell of his cock to bring attention to your own sex, damp and throbbing with desire in a way that no mere fantasy could satisfy.

Unable to contain the strangled moan that leaves your throat, you swim with the current, grasping him tightly through his boxers.

“Feel that, baby?” he rasps against your ear. “That's all you.”

His words cause an abrupt clench of the muscles deep within your heat, mimicking the firm grip of your hand around him, and you yearn to replace one with the other.

“Fuck me, Dean. Now. _Please._ ” In one stroke, you release his cock, bringing both of your arms up to drape around his neck.

With an urgency matching your own, he slides his hands over your ass, giving a marked squeeze before yanking your panties down over your curves. You've never been more grateful for the easy access of a short skirt—“not exactly practical” for a hunt, sure, but invaluable here. A wiggle of your hips brings your panties the rest of the way to the floor and you step out of them, making room for the eager hand Dean presses between your thighs.

Two coarse fingers drag across the entirety of your slick folds. “So wet for me,” he breathes, giving you a forceful, predatory kiss against your lips before whispering an oath of indulgence against them: “I've got everything you need.”

Making good on his word, he tugs down his jeans and boxers, just enough that every flawless inch of his cock springs free. Strong hands at the back of your thighs give him leverage to lift you up, your legs wrapping instinctively around his waist as he steadies you against the wall and uses one hand to line up the head of his cock with your entrance. He glances up at you, begging your permission with his eyes—dark green, stormy, and dangerous.

All you can manage is a curt nod of your head before he thrusts himself into you, eliciting a simultaneous pair of enraptured curses. Once inside the tight confines of your cunt, Dean is utterly unbound, every pretense of patience and restraint replaced with sheer, carnal impulse.

He grips your ass tightly with each of his large hands, the cool silver of his ring a brief but stimulating contrast against your hot skin. Adjusting your body to a new angle, he pumps into you hard and fast.

 _Too many clothes_ , you think, wishing you could see the sinuous tensing and flexing of the muscles in his arms as he holds you in place. _Next time, less clothes._ One encore performance had already been promised, but with the gratuitous way he fills you up and whispers obscenities into your ear, you hope it won't be the last.

“Fuck, Y/N,” he swears between ragged gasps, his thick cock stretching you to the fine edge of bliss, bottoming out with each upward push. “You feel so good—so damn good.”

You press your bare breasts against his sturdy chest, the textured cotton of his shirt feeling exquisite as it brushes against your nipples with each of his motions. In an effort to silence your amorous whines, you take his bottom lip between both of your own, sucking gently until he offers his tongue instead. To it, you grant an even more vulgar display of attention, rolling your own tongue in a colliding tempo that matches the frantic bucking of his hips.

Your back now flat against the wall, Dean draws closer, the very definition of intimacy: grinding every inch of himself against every inch of you. Each movement of your writhing body against his provides blissful, much-needed pressure to your swollen clit.

It's not long before his unrelenting rhythm has you perched on the verge of orgasm, and you pull back panting, dizzy for air. “Gonna—gonna come,” you whimper, burying your face in the crook of his neck, breathing in the same piney scent you'd found so appealing before.

“That's right,” he grunts, the furious pace of his thrusts now feral and aggressive. “Come for me. Wanna hear you scream my name.”

At the mercy of your own pleasure, there's no way you can resist, shouting a euphoric “ _Dean!_ ” with each resounding pulse of your orgasm as you tighten and come around him.

Pulled over the ledge with you, he gives in to his own satisfaction, cock twitching and filling you with his warm release. A litany of curse words falls from his lips, made beautiful by the alternating gasps of your name.

After a moment's rest in a locked embrace, he helps you down, letting you balance yourself despite the shaking of your legs. You tug your displaced halter back down and grab your discarded panties, relegating them to clean-up duty before heading back to the desk to grab a pair of jeans out of your bag.

“So?” Dean asks, the room all of a sudden too silent without the resonating chorus of passionate cries. He brings himself back to decency and fastens his belt, giving a purposeful tilt of his head toward the computer. “The book or the movie?”

“The movie,” you reply, grinning up at him as you remove your boots and skirt. “Definitely.”

He rewards the answer with a smile of his own that reaches his eyes, causing them to crease at the corners—a simple detail, but one you'd fallen in love with so many times before. And then buried under layers of deep, deep denial. Naturally.

“Full disclosure, Dean,” you add, while dressing yourself back up in your jeans and boots, the bottom half of your _Supernatural_ garb now balled up and stuffed in your pack. “I was kinda hoping you'd find the 'Y/N' costume hot.”

“Honestly? It was a little hot,” he says with a flirty smirk and raised eyebrows—one of the many charming expressions that had been sorely absent from his face for the past month.

God, you'd missed it.

“But the real you?” He pulls you close, giving you one last lingering kiss. “So much better.”

**Author's Note:**

> I can also be found on Tumblr as [white-feather-black-ink](http://white-feather-black-ink.tumblr.com). Bonus: everything I post there comes with a handy little button that will replace all the Y/N tags in the story with your name (or whatever name you choose to enter). If you'd like to follow me there, please feel free. Thanks for reading!


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